Secrets of Writing Difficult Letters

Date: February 1, 2004      Publication: Bottom Line Publications      Source: Rosalie Maggio      Print:

I’ve never seen such a proliferation of books on letter writing, anthologies of correspondence and books of letters by the famous — all at a time when fewer people than ever are writing letters.

We needn’t abandon the graciousness and etiquette of previous generations just because we’re “busy.”

When you write a letter, you create good feelings and feel good about yourself. The fact of your writing is more important than what you write. The recipient will be glad to receive anything personal among the daily avalanche of bills and junk mail. If most people realized how glad, they would write more.

Bonus: Letter writing can be a fine outlet for communicating with (and by) the hard of hearing.

Example: For my elderly father, who has trouble hearing, talking on the phone is no longer the joy it once was. Instead, he sends letters and E-mail messages to family members and friends.


People often ask me which kind of letter is most difficult to write. I think it’s the one that’s been put off. The longer you let it sit, the more you dread thinking about it.

The letter you set aside looms larger and larger every day. It may not get written, or if it is — not written well.

In his delightful book on manners for teens, How Rude!, Alex J. Packer exaggerates only a little when he writes, “Thank-you notes get exponentially more difficult to write with each day that passes. By the second day, they are four times harder to write. By the third day, they are nine times harder, and if you wait 12 days, they are 144 times harder to write!”

Surprisingly helpful: I divide my letters requiring a reply into three piles — those that can wait indefinitely… those that don’t have to be answered this week…and those that must be answered this week. Thinking about the whole pile overwhelms me, but getting a couple of urgent letters in the mail always seems possible.

Don’t feel you have to write three times as much or four times as charmingly because you’re late. The pressure will prevent you from writing. Write what you would have written if you had written sooner. Be honest — say you have no excuse and are sorry for the delay.


When my mother died recently, I was astonished at how much the notes comforted my family and me. No two of the 800-plus commercial sympathy cards we received were alike, and none contained simply a signature. Everyone had written at least one line under the message.

People wrote promptly and to the point: “We were so sorry to hear of the loss of your mother [or, to my father, “your wife”]. She was a wonderful woman.” None of us — not Dad, not any of us eight siblings — stopped to analyze the writer’s grammar or phrasing. What we cared about was that people had made the effort.


Writing letters you don’t have to write can help get you in the mood. Make a habit of sending notes of congratulation or appreciation. A note of appreciation is one of the most pleasant to receive because we do not expect it and one of the most satisfying to write because we are not obliged to send it.

Mary Kay Ash, founder of Mary Kay Cosmetics, said, “Everyone wants to be appreciated. If you appreciate someone, don’t keep it a secret.”

In the process, you will have established the habit of writing, complete with a supply of note cards and other stationery.


Focus on the recipient. You may be feeling inadequate in the face of death or serious illness, embarrassed about a faux pas for which you must apologize or irritated about having to thank someone for a useless gift. Set your negative feelings aside. Focus on what you want your recipient to hear: “I’m thinking about you.” “How good of you to think of me.” “I’m counting on you to forgive me.”

Think before you write. When we’re stumped, we aren’t clear in our own minds about what we want to write. Say your message aloud as though speaking to a friend. On scratch paper, jot down the message you want to get across. In a difficult letter, the message is usually simple: “I’m sorry.” “Thank you.” Write just that, elaborate a bit and you’ll have your note.

Review the letter. Let any potentially prickly letter sit for a day before mailing it. Show it to someone you trust, and ask for a frank opinion.

Send a card. When the prospect of sending a letter is overwhelming, rely on the incredible array of commercial greeting cards. It’s far better to send a card than to send nothing. Choose your card with care and always, always add a line or two.

Send an E-mail. I have received messages of sympathy and thanks by E-mail from people with whom I communicate primarily by E-mail. But there is no substitute for “snail mail.” A letter of congratulations elevates the situation. A handwritten note communicates respect and acknowledges an event’s importance.

Admit your reluctance to yourself. Sometimes it helps to say out loud: “I don’t like writing letters. I’m not good at it. I don’t want to write this letter.” Take a moment to sigh. Then pull an envelope toward you, address it and get started.

Also helpful: Keep note paper, stamped picture postcards and a pen near the TV to write letters during commercials… near the phone, to jot down thoughts while “on hold”… in the kitchen, to use while dinner cooks.

Source: Rosalie Maggio, award-winning author of the best-seller How to Say It: Choice Words, Phrases, Sentences, and Paragraphs for Every Occasion (Prentice Hall/Perigee). She is based in Frazier Park, California.